Decarboxylative Tribromination for the Selective Synthesis of Tribromomethyl Ketone and Tribromovinyl Derivatives
作者:Aravindan Jayaraman、Eunjeong Cho、Jimin Kim、Sunwoo Lee
DOI:10.1002/adsc.201800851
日期:2018.10.18
Tribromomethyl ketone and tribromovinyl derivatives were selectively prepared from the decarboxylative tribromination. The reaction between propiolic acid derivatives and dibromoisocyanuric acid (DBCA)/H2O afforded predominantly a tribromomethyl ketone derivative in the presence of AgOAc (10 mol%). When the same reaction was conducted with 2,2,6,6‐tetramethyl‐1‐piperidinyloxy (TEMPO) instead of AgOAc
由脱羧三溴化作用选择性地制备三溴甲基酮和三溴乙烯基衍生物。在AgOAc(10mol%)存在下,丙酸衍生物与二溴异氰尿酸(DBCA)/ H 2 O之间的反应主要得到三溴甲基酮衍生物。当用2,2,6,6-四甲基-1-哌啶基氧基(TEMPO)代替AgOAc进行相同的反应时,仅以高收率形成了三溴乙烯基衍生物。发现乙炔基溴是中间体。